Compound for organic electric element, organic electric element using the same, and an electronic device thereof

ABSTRACT

The present invention provides the compound represented by Formula 1, an organic electric element comprising a first electrode, a second electrode, and an organic material layer formed between the first electrode and the second electrode, and electronic device thereof, and by employing the compound represented by Formula 1 in the organic material layer, the driving voltage of the organic electric element can be lowered, and the luminous efficiency and life time of the electric element can be improved.

CROSS-REFERENCE TO RELATED APPLICATION

This patent application claims priority from and the benefit under 35U.S.C. § 119 to § 121, and § 365 of Korean Patent Application No.10-2018-0006547, filed on Jan. 18, 2018 which is hereby incorporated byreference for all purposes as if fully set forth herein. Further, thisapplication claims the benefit of priority in countries other than U.S.,which is hereby incorporated by reference herein.

BACKGROUND Technical Field

The present invention relates to compound for an organic electricelement, an an organic electric element using the same and an electronicdevice thereof.

Background Art

In general, an organic light emitting phenomenon refers to a phenomenonthat converts electric energy into light energy using an organicmaterial. An organic electric element utilizing the organic lightemitting phenomenon usually has a structure comprising an anode, acathode, and an organic material layer formed the anode and the cathode.In many cases, the organic material layer has a multi-layered structurehaving respectively different materials in order to improve efficiencyand stability of an organic electric element, and for example, maycomprise a hole injection layer, a hole transport layer, a lightemitting layer, an electron transport layer, an electron injection layerand the like.

Materials used as an organic material layer in an organic electricelement may be classified into a light emitting material and a chargetransport material, for example, a hole injection material, a holetransport material, an electron transport material, an electroninjection material and the like according to its function.

Currently, the power consumption is required more than more as the sizeof display becomes larger and larger in the portable display market.Therefore, the power consumption is a very important factor in theportable display with a limited power source of the battery, andefficiency and life span issue also is solved.

Efficiency, life span, driving voltage, and the like are correlated witheach other. if efficiency is increased, then driving voltage isrelatively lowered, and the crystallization of an organic material dueto Joule heating generated during operation is reduced as drivingvoltage is lowered, as a result of which life span shows a tendency toincrease. However, efficiency cannot be maximized only by simplyimproving the organic material layer. This is because long life span andhigh efficiency can be simultaneously achieved when an optimalcombination of energy levels and T₁ values, inherent material properties(mobility, interfacial properties, etc.), and the like among therespective layers included in the organic material layer is given.

In addition, in the recent organic electroluminescent devices, anemission-auxiliary layer (multi-layered hole transport layer) must bepresent between the hole transport layer and the light emitting layer inorder to solve the problems of luminescence in the hole transport layerand the driving voltage, and it is necessary to develop differentemission-auxiliary layers according to respective light emitting layers.

In general, an electron is transferred from an electron transport layerto a light emitting layer and a hole is transferred from a holetransport layer to the light emitting layer, as a result, an exciton isformed by the recombination of the electron and hole within the lightemitting layer.

However, material used in a hole transport layer has a low T1 valuebecause the material should have a low HOMO value. As a result, theexciton generated in the light emitting layer is transferred to the holetransport layer and it causes charge unbalance in the light emittinglayer, thereby emitting light at the interface of the hole transportlayer.

When light is emitted from the interface of a hole transporting layer,the color purity and efficiency of the organic electronic element arelowered and the lifetime is shortened. Therefore, it is strongly desiredto develop materials for the emission-auxiliary layer having a HOMOlevel between the HOMO energy level of the hole transporting layer andthe HOMO energy level of the light emitting layer, a high T1 energyvalue and a hole mobility within a suitable driving voltage range(within a driving voltage range of blue element of a full device).

However, this cannot be achieved simply by the structural properties ofthe core of the emission-auxiliary layer material. An element having ahigh efficiency and a long life span can be realized when thecharacteristics of core and sub-substituents of the emission-auxiliarylayer material, the proper combination of the emission-auxiliary layerand the hole transport layer, and the proper combination of theemission-auxiliary layer and the light emitting layer.

In order to fully exhibit the excellent characteristics of the organicelectric element, materials forming the organic material layer in theelement, such as a hole injection material, a hole transport material, alight emitting material, an electron transport material, an electroninjection material, an emission-auxiliary layer material, etc. should beprerequisite to support by a stable and efficient material, inparticular, it is strongly required to develop material for anemission-auxiliary layer.

Object, Technical Solution and Effects of the Invention

An object of the present invention is to provide a compound lowering adriving voltage, improving luminous efficiency, color purity andlifetime of the element, an organic electric element using the same, andan electronic device thereof.

In an aspect of the present invention, the present invention providesthe compound represented by the following formula.

In another aspect of the present invention, the present inventionprovides an organic electric element employing the compound representedby formula above and an electronic device thereof.

By using the compound according to embodiment of the present invention,a driving voltage of an organic electric element can be lowered and theluminous efficiency, color purity and lifetime of the element can belargely improved.

BRIEF DESCRIPTION OF THE DRAWINGS

FIGURE illustrates an example of an organic electroluminescent elementaccording to the present invention: 100 is an organic electric element,110 is a substrate, 120 is a first electrode, 130 is a hole injectionlayer, 140 is a hole transport layer, 141 is a buffer layer, 150 is alight emitting layer, 151 is an emission-auxiliary layer, 160 is anelectron transport layer, 170 is an electron injection layer, and 180 isa second electrode.

DETAILED DESCRIPTION

In this specification, a ‘group name’ corresponding to an aryl group, anarylene group, a heterocyclic group, and the like exemplified for eachsymbol and its substituent may be written in the name of functionalgroup reflecting the valence, and may also be described as the name of aparent compound. For example, in the case of phenanthrene which is akind of aryl group, it may be described by distinguishing valence suchas ‘phenanthryl’ when it is ‘monovalent group’, and as ‘phenanthrylene’when it is ‘divalent group’, and it may also be described as a parentcompound name, ‘phenanthrene’, regardless of its valence. Similarly, inthe case of pyrimidine, it may be described as ‘pyrimidine’ regardlessof its valence, and it may also be described as the name ofcorresponding functional group such as pyrimidinyl when it is‘monovalent group’, and as ‘pyrimidylene’ when it is ‘divalent group’.

Unless otherwise stated, the term “fluorenyl group” or “fluorenylenegroup” as used herein means univalent or bivalent functional group inwhich R, R′ and R″ are all hydrogen in the following structure,“substituted fluorenyl group” or “substituted fluorenylene group” meansthat at least any one of R, R′ and R″ is a substituent other thanhydrogen, and it comprises the case where R and R′ are bonded to eachother to form the spiro compound together with the carbon to which theyare bonded.

The term “spiro compound” as used herein has, a spiro union which meansunion having one atom as the only common member of two rings. The commonatom is designated as ‘spiro atom’. The compounds are defined as‘monospiro-’, ‘dispiro-’ or ‘trispiro-’ depending on the number of Spiroatoms in one compound.

The term “heterocyclic group” as used herein means a ring comprising aheteroatom like N, O, S, P, Si or the like instead of carbon consistingof, it comprises a non-aromatic ring as well as an aromatic ring like“heteroaryl group” or “heteroarylene group” and the compound comprisingthe heteroatom group like SO₂, P═O or the like instead of carbonconsisting of a ring such as the following compound.

In addition, otherwise specified, the formulas used in the presentinvention are as defined in the index definition of the substituent ofthe following formula.

Here, the substituent R¹ is absent when a is an integer of zero, thesole R¹ is bonded to any one of the carbon atoms constituting thebenzene ring when a is an integer of 1, when a is an integer of 2 or 3,the substituent R¹s may be bonded as follows and the substituents R¹smay be the same or different each other, and the substituent R¹s may bebonded to the carbon of the benzene ring in a similar manner when a isan integer of 4 to 6. Herein, the indication of the hydrogen bonded tothe carbon which forms the benzene ring is omitted.

Hereinafter, a laminated structure of the electric element comprisingthe compound of the present invention will be described with referenceto FIGURE.

The FIGURE illustrates a laminated structure of an organic electricelement according to an embodiment of the present invention.

Referring to the FIGURE, an organic electric element 100 according to anembodiment of the present invention includes a first electrode 120, asecond electrode 180, and an organic material layer formed between thefirst electrode 120 and the second electrode 180 and comprising thecompound of the present invention which are formed on a substrate 110.Here, the first electrode 120 may be an anode (positive electrode), andthe second electrode 180 may be a cathode (negative electrode). In thecase of an inverted organic electroluminescent element, the firstelectrode may be a cathode, and the second electrode may be an anode.

The organic material layer may include a hole injection layer 130, ahole transport layer 140, a light emitting layer 150, an electrontransport layer 160, and an electron injection layer 170 formed insequence on the first electrode 120. Here, at least one layer of theorganic material layer may be omitted, or the organic material layer mayfurther include a hole blocking layer, an electron blocking layer, anemission-auxiliary layer 151, an electron transport-auxiliary layer, abuffer layer 141, etc., and the electron transport layer 160 or the likemay serve as a hole blocking layer.

In addition, although not shown, the organic electric element accordingto an embodiment of the present invention may further include aprotective layer or a layer for improving luminous efficiency formed onat least one side of both sides of the first electrode and the secondelectrode, wherein at least one side is not facing the organic materiallayer.

The inventive compound employed in the organic material layer may beused as a material of a hole injection layer 130, a hole transport layer140, an emission-auxiliary layer 151, an electron transport-auxiliarylayer, an electron transport layer 160, an electron injection layer 170and the like, host or dopant for a light emitting layer 150, or materialof a layer for improving luminous efficiency. For example, the inventivecompound may be used as material for a hole transport layer 140 and/oran emission-auxiliary layer 151, preferably, or an emission-auxiliarylayer 151.

On the other hand, even if the core is same, the band gap, theelectrical characteristics, the interface characteristics and the likemay be different depending on which substituent is bonded at whichposition. Therefore, there is a need to study the selection of the coreand the combination of the core and the sub-substituent bonded to thecore. In particular, long life span and high efficiency can besimultaneously achieved when the optimal combination of energy levelsand T₁ values, inherent material properties (mobility, interfacialproperties, etc.) and the like among the respective layers of an organicmaterial layer is achieved.

Therefore, the energy level and T₁ value between the respective layersof the organic material layer, inherent material properties (mobility,interfacial properties, etc.) and the like can be optimized by formingan emission-auxiliary layer 151 with the compound of the presentinvention, and thus it is possible to simultaneously improve the lifespan and efficiency of the organic electric element.

The organic electric element according to an embodiment of the presentinvention may be manufactured using various deposition methods. Theorganic electric element according to an embodiment of the presentinvention may be manufactured using a PVD (physical vapor deposition)method or CVD (chemical vapor deposition) method. For example, theorganic electric element may be manufactured by depositing a metal, aconductive metal oxide, or a mixture thereof on the substrate to formthe anode 120, forming the organic material layer including the holeinjection layer 130, the hole transport layer 140, the light emittinglayer 150, the electron transport layer 160, and the electron injectionlayer 170 thereon, and then depositing a material, which can be used asthe cathode 180, thereon. In addition, an emitting auxiliary layer 151may be formed between a hole transport layer 140 and a light emittinglayer 150, and an electron transport-auxiliary layer may be formedbetween a light emitting layer 150 and an electron transport layer 160.

In addition, the organic material layer may be manufactured in such amanner that a smaller number of layers are formed using various polymermaterials by a soluble process or solvent process, for example, spincoating, nozzle printing, inkjet printing, slot coating, dip coating,roll-to-roll, doctor blading, screen printing, or thermal transfer,instead of deposition. Since the organic material layer according to thepresent invention may be formed in various ways, the scope of protectionof the present invention is not limited by a method of forming theorganic material layer.

The organic electric element according to the present invention may beone of an organic light emitting device (OLED), an organic solar cell,an organic photo conductor (OPC), an organic transistor, an element formonochromatic or white illumination and an element quantum dot display.

Another embodiment of the present invention provides an electronicdevice including a display device which includes the above describedorganic electric element, and a control unit for controlling the displaydevice. Here, the electronic device may be a wired/wirelesscommunication terminal which is currently used or will be used in thefuture, and covers all kinds of electronic devices including a mobilecommunication terminal such as a cellular phone, a personal digitalassistant (PDA), an electric dictionary, a point-to-multipoint (PMP), aremote controller, a navigation unit, a game player, various kinds ofTVs, and various kinds of computers, and the display device may comprisean electroluminescent display, a quantum dot display and so on.

Hereinafter, the compound according to an aspect of the presentinvention will be described.

Compound according to an aspect of the present invention may berepresented by Formula 1.

In formula 1, each of symbols may be defined as follows.

Ar₁ and Ar₂ are each independently selected from the group consisting ofa C₆-C₆₀ aryl group, a C₂-C₆₀ heterocyclic group containing at least oneheteroatom of O, N, S, Si, and P, a C₃-C₆₀ aliphatic ring group, aC₁-C₅₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynyl group, aC₁-C₃₀ alkoxyl group, a C₆-C₃₀ aryloxy group, and -L′-N(R_(a))(R_(b)),and adjacent groups together may be bonded to each other to form aheterocyclic group containing Si.

Where Ar₁ and Ar₂ are an aryl group, the aryl group may be preferably aC₆-C₃₀, more preferably a C₆-C₁₄ aryl group, for example, phenyl,biphenyl, naphthyl, phenanthrene and the like. Where Ar₁ and Ar₂ are aheterocyclic group, the heterocyclic group may be preferably a C₂-C₃₀,more preferably a C₂-C₈ heterocyclic group, for example, pyridine,pyrimidine, triazine, quinazoline and the like. Where Ar₁ and Ar₂ are analkyl group, the alkyl group may be preferably a C₁-C₁₀ alkyl group,more preferably a C₁-C₄ alkyl group, for example, methyl, ethyl, t-butyland the like. In addition, where Ar₁ and Ar₂ are bonded to each other toform a ring, the ring may be a spiro-compound together with the Si towhich they are attached, wherein the spiro-atom is Si.

Ar₃ to Ar₆ are each independently selected from the group consisting ofa C₆-C₆₀ aryl group, a C₂-C₆₀ heterocyclic group containing at least oneheteroatom of O, N, S, Si, and P, a C₃-C₆₀ aliphatic ring group,-L′-N(R_(a))(R_(b)) and Formula 1-1, and adjacent groups together may bebonded to each other to form a C₂-C₆₀ heterocyclic group containing N.With the proviso that at least one of Ar₃ to Ar₆ is Formula 1-1.

Where Ar₃ to Ar₆ are an aryl group, the aryl group may be preferably aC₆-C₃₀, more preferably a C₆-C₁₈ aryl group, for example, phenyl,biphenyl, naphthyl, phenanthrene, triphenylene, terphenyl and the like.Where Ar₃ to Ar₆ are a heterocyclic group, the heterocyclic group may bepreferably a C₂-C₃₀, more preferably a C₂-C₂₂ heterocyclic group, forexample, pyridine, pyrimidine, dibenzothiophene, dibenzofuran,carbazole, phenylcarbazole, 9-(naphthalen-2-yl)-9H-carbazole,benzonaphthofuran and the like. Where Ar₃ to Ar₆ are a fluorenyl group,the fluorenyl group may be dimethylfluorene, diphenylfluorene and thelike.

X is O or S.

R₁ to R₄ are each independently selected from the group consisting ofhydrogen, deuterium, halogen, a C₆-C₆₀ aryl group, a fluorenyl group, aC₂-C₆₀ heterocyclic group containing at least one heteroatom of O, N, S,Si, and P, a C₃-C₆₀ aliphatic ring group, a C₁-C₅₀ alkyl group, a C₂-C₂₀alkenyl group, a C₁-C₃₀ alkoxyl group, a C₆-C₃₀ aryloxy group and-L′-N(R_(a))(R_(b)), and adjacent groups together may be bonded to eachother to form a ring.

Adjacent R₁s, adjacent R₂s, adjacent R₃s or adjacent R₄s together may bebonded to each other to form a ring, wherein the ring is selected fromthe group consisting of a C₆-C₆₀ aromatic ring, a fluorenyl group, aC₂-C₆₀ heterocyclic group containing at least one heteroatom of O, N, S,Si, and P, a C₃-C₆₀ aliphatic ring group, and a combination thereof.Where adjacent groups together may be bonded to each other to form anaromatic ring, the aromatic ring is preferably a C₆-C₂₀, more preferablya C₆-C₁₀ aromatic ring, for example, benzene, naphthalene and the like.

Where R₁ to R₄ are an aryl group, the aryl group may be preferably aC₆-C₃₀, more preferably a C₆-C₁₂ aryl group, for example, phenyl,biphenyl, naphthyl and the like. Where R₁ to R₄ are an aliphatic ringgroup, the aliphatic ring group may be preferably a C₃-C₃₀, morepreferably a C₃-C₆ aliphatic ring group, for example, cyclohexane.

n, m and o are each an integer of 0 to 3, l is an integer of 0˜4, wherethey are each an integer of 2 or more, each of a plurality of R₁s, eachof a plurality of R₂s, each of a plurality of R₃s, each of a pluralityof R₄s are the same or different from each other.

L₁, L₂ and L are each independently selected from the group consistingof a single bond, a C₆-C₆₀ arylene group, a fluorenylene group, a C₂-C₆₀heterocyclic group containing at least one heteroatom of O, N, S, Si,and P, and a C₃-C₆₀ aliphatic ring. Where L₁, L₂ and L are an arylenegroup, the arylene group may be preferably a C₆-C₃₀, more preferably aC₆-C₁₂ arylene group, for example, phenylene, biphenyl, naphthalene andthe like.

L′ is selected from the group consisting of a single bond, a C₆-C₆₀arylene group, a fluorenylene group, a C₃-C₆₀ aliphatic ring and aC₂-C₆₀ heterocyclic group.

R_(a) and R_(b) are each independently selected from the groupconsisting of a C₆-C₆₀ aryl group, a fluorenyl group, a C₃-C₆₀ aliphaticring group, and a C₂-C₆₀ heterocyclic group containing at least oneheteroatom of O, N, S, Si, and P.

Ar₁ to Ar₆, R₁ to R₄, the ring formed by adjacent groups, L₁, L₂, L, L′,R_(a) and R_(b) may be each optionally substituted with one or moresubstituents selected from the group consisting of deuterium, halogen, asilane group unsubstituted or substituted with a C₁-C₂₀ alkyl group or aC₆-C₂₀ aryl group, a siloxane group, a boron group, a germanium group, acyano group, a nitro group, a phosphine oxide group unsubstituted orsubstituted with a C₁-C₂₀ alkyl group or a C₆-C₂₀ aryl group, a C₁-C₂₀alkylthio group, a C₁-C₂₀ alkoxyl group, a C₁-C₂₀ alkyl group, a C₂-C₂₀alkenyl group, a C₂-C₂₀ alkynyl group, a C₆-C₂₀ aryl group, a C₆-C₂₀aryl group substituted with deuterium, a fluorenyl group, a C₂-C₂₀heterocyclic group containing at least one heteroatom of O, N, S, Si,and P, a C₃-C₂₀ cycloalkyl group, a C₇-C₂₀ arylalkyl group, and C₈-C₂₀arylalkenyl group.

For example, Ar₁ to Ar₆ are further substituted with methyl, ethene,pyridine, methoxy, phenyl, F and the like.

Preferably, Formula 1 may be represented by Formula 2 or Formula 3.

In Formulas 2 and 3, X, Ar₁ to Ar₅, R₁ to R₄, L₁, L₂, n, m, o and l arethe same as defined for Formula 1.

In addition, Formula 1 may be represented by one of Formula 4 to Formula7.

In Formulas 4 to 7, Ar₁ to Ar₆, R₁, R₂, L₁, L₂, n and m are the same asdefined for Formula 1.

In addition, Formula 1 may be represented by one of Formula 8 to Formula10.

In Formulas 8 to 10, Ar₁ to Ar₆, R₁, R₂, L₁, L₂, n and m are the same asdefined for Formula 1.

Specifically, compound represented by formula 1 may be one of thefollowing compounds.

In another aspect of the present invention, the present inventionprovides an organic electric element comprising a first electrode, asecond electrode, and an organic material layer formed between the firstelectrode and the second electrode, wherein the organic material layercomprises a single compound two or more compounds represented by Formula1.

The organic material layer comprises at least one of a hole injectionlayer, a hole transport layer, an emission-auxiliary layer, a lightemitting layer, an electron transport-auxiliary layer, an electrontransport layer and an electron injection layer, preferably, thecompound is comprised in the emission-auxiliary layer or the holetransport layer.

In another aspect of the present invention, the present inventionprovides an electronic device comprising a display device and a controlunit for driving the display device, wherein the display devicecomprises the organic electric element.

Hereinafter, synthesis example of the compound represented by Formula 1and preparation method of an organic electroluminescent elementaccording to the present invention will be described in detail by way ofexamples. However, the present invention is not limited to the followingexamples.

Synthesis Example

The compound represented by Formula 1 according to the present inventioncan be synthesized by reacting Sub 1 with Sub 2.

Synthesis Example

The compound represented by Formula 1 according to the present inventioncan be synthesized by reacting Sub 1 and Sub 2 as shown in ReactionScheme 1 below.

Synthesis Example of Sub 1

Sub 1 of Reaction Scheme 1 can be synthesized by the reaction route ofReaction Scheme 2 below, but there is no limitation thereto.

Synthesis example of compound belong to Sub 1 is as follows.

1. Synthesis Example of Sub 1-1

2-bromo-7-chloro-5,5-diphenyl-5H-dibenzo[b,d]silole (15 g, 0.033 mol),N-phenyldibenzo[b,d]thiophen-2-amine (9.2 g, 0.033 mol), Pd₂(dba)₃ (0.9g, 0.001 mol), (t-Bu)₃P (0.8 mL, 0.002 mol) and NaOt-Bu (9.6 g, 0.10mol) were added to anhydrous toluene (67 mL) and the reaction wascarried out for 4 hours. When the reaction was completed, the reactionproduct was extracted with CH₂Cl₂ and water, the organic layer was driedwith MgSO₄ and concentrated. Thereafter, the concentrate was separatedby a silica gel column and recrystallized to obtain 18 g (yield: 83%) ofproduct Sub 1-1.

2. Synthesis Example of Sub 1-5

The reaction was carried out in the same manner as in the synthesismethod of Sub 1-1 using2-bromo-7-chloro-5,5-diphenyl-5H-dibenzo[b,d]silole (40 g, 0.09 mol),diphenylamine (15.1 g, 0.09 mol), Pd₂(dba)₃ (2.45 g, 0.002 mol),(t-Bu)₃P (2.1 mL, 0.004 mol), NaOt-Bu (25.8 g, 0.278 mol) and anhydroustoluene (180 mL) to obtain 38 g (yield: 79%) of product Sub 1-5.

3. Synthesis Example of Sub 1-22

The reaction was carried out in the same manner as in the synthesismethod of Sub 1-1 using3-bromo-7-chloro-5,5-dimethyl-5H-dibenzo[b,d]silole (40 g, 0.12 mol),N-phenyldibenzo[b,d]furan-3-amine (32 g, 0.12 mol), Pd₂(dba)₃ (3.4 g,0.003 mol), (t-Bu)₃P (3.1 mL, 0.006 mol), NaOt-Bu (35 g, 0.37 mol) andanhydrous toluene (250 mL) to obtain 55 g (yield: 89%) of product Sub1-22.

4. Synthesis Example of Sub 1-26

The reaction was carried out in the same manner as in the synthesismethod of Sub 1-1 using3-(3-(2-bromo-8-chloro-5-phenyl-5H-dibenzo[b,d]silol-5-yl)phenyl)pyridine(10 g, 0.02 mol), diphenylamine (3.2 g, 0.02 mol), Pd₂(dba)₃ (0.5 g,0.0006 mol), (t-Bu)₃P (0.4 mL, 0.0012 mol), NaOt-Bu (5.5 g, 0.06 mol)and anhydrous toluene (38 mL) to obtain 8 g (yield: 68.5%) of productSub 1-26.

5. Synthesis Example of Sub 1-39

The reaction was carried out in the same manner as in the synthesismethod of Sub 1-1 using10-bromo-5-chloro-7,7-diphenyl-7H-benzo[b]naphtho[1,2-d]silole (30 g,0.06 mol), diphenylamine (10.1 g, 0.06 mol), Pd₂(dba)₃ (1.7 g, 0.002mol), (t-Bu)₃P (1.4 mL, 0.002 mol), NaOt-Bu (17.4 g, 0.18 mol) andanhydrous toluene (120 mL) to obtain 30 g (yield: 85%) of product Sub1-39.

6. Synthesis Example of Sub 1-59

The reaction was carried out in the same manner as in the synthesismethod of Sub 1-1 using8-bromo-1-chloro-5,5-diphenyl-5H-dibenzo[b,d]silole (30 g, 0.07 mol),(4-(diphenylamino)phenyl)boronic acid (19.3 g, 0.07 mol), Pd₂(dba)₃ (1.7g, 0.002 mol), (t-Bu)₃P (1.4 mL, 0.002 mol), NaOt-Bu (17.4 g, 0.18 mol)and anhydrous toluene (120 mL) to obtain 32 g (yield: 78%) of productSub 1-59.

Compounds belonging to Sub 2 may be, but not limited to, the followingcompounds, and Table 1 shows FD-MS (Field Desorption-Mass Spectrometry)values of the following compounds.

TABLE 1 Compound FD-MS Compound FD-MS Sub 1-1 m/z = 641.14 (C₄₂H₂₈ClNSSi= 642.29) Sub 1-2 m/z = 641.14 (C₄₂H₂₈ClNSSi = 642.29) Sub 1-3 m/z =625.16 (C₄₂H₂₈ClNOSi = 626.23) Sub 1-4 m/z = 625.16 (C₄₂H₂₈ClNOSi =626.23) Sub 1-5 m/z = 535.15 (C₃₆H₂₆ClNSi = 536.15) Sub 1-6 m/z = 745.20(C₅₀H₃₆ClNSSi = 746.44) Sub 1-7 m/z = 593.14 (C₃₈H₂₈ClNSSi = 594.24) Sub1-8 m/z = 853.26 (C₆₀H₄₀ClNOSi = 854.52) Sub 1-9 m/z = 675.18(C₄₆H₃₀ClNOSi = 676.29) Sub 1-10 m/z = 563.18 (C₃₈H₃₀ClNSi = 564.20) Sub1-11 m/z = 563.18 (C₃₈H₃₀ClNSi = 564.20) Sub 1-12 m/z = 631.16(C₄₁H₃₀ClNSSi = 632.29 Sub 1-13 m/z = 531.12 (C₃₃H₂₆ClNSSi = 532.17) Sub1-14 m/z = 621.13 (C₃₉H₂₈ClNOSSi = 622.25) Sub 1-15 m/z = 515.15(C₃₃H₂₆ClNOSi = 516.11) Sub 1-16 m/z = 411.12 (C₂₆H₂₂ClNSi = 412.00) Sub1-17 m/z = 535.15 (C₃₆H₂₆ClNSi = 536.15) Sub 1-18 m/z = 439.15(C₂₈H₂₆ClNSi = 440.06) Sub 1-19 m/z = 747.13 (C₄₈H₃₀ClNS₂Si = 748.43)Sub 1-20 m/z = 579.12 (C₃₇H₂₆ClNSSi = 580.22) Sub 1-21 m/z = 729.19(C₄₉H₃₂ClNO₂Si = 730.34) Sub 1-22 m/z = 501.13 (C₃₂H₂₄ClNOSi = 502.09)Sub 1-23 m/z = 535.15 (C₃₆H₂₆ClNSi = 536.15) Sub 1-24 m/z = 700.21(C₄₈H₃₃ClN₂Si = 701.34) Sub 1-25 m/z = 701.19 (C₄₈H₃₂ClNOSi = 702.33)Sub 1-26 m/z = 612.18 (C₄₁H₂₉ClN₂Si = 613.23) Sub 1-27 m/z = 595.17(C₃₈H₃₀ClNO₂Si = 596.20) Sub 1-28 m/z = 626.19 (C₄₂H₃₁ClN₂Si = 627.26)Sub 1-29 m/z = 501.13 (C₃₂H₂₄ClNOSi = 502.09) Sub 1-30 m/z = 635.18(C₄₄H₃₀ClNSi = 636.27) Sub 1-31 m/z = 576.18 (C₃₈H₂₉ClN₂Si = 577.20) Sub1-32 m/z = 662.19 (C₄₅H₃₁ClN₂Si = 663.29) Sub 1-33 m/z = 501.17(C₃₃H₂₈ClNSi = 502.13) Sub 1-34 m/z = 551.15 (C₃₆H₂₆ClNOSi = 552.15) Sub1-35 m/z = 638.19 (C₄₃H₃₁ClN2Si = 639.27) Sub 1-36 m/z = 517.11(C₃₂H₂₄ClNSSi = 518.15) Sub 1-37 m/z = 501.13 (C₃₂H₂₄ClNOSi = 502.09)Sub 1-38 m/z = 676.21 (C₄₆H₃₃ClN2Si = 677.32) Sub 1-39 m/z = 585.17(C₄₀H₂₈ClNSi = 586.21) Sub 1-40 m/z = 643.16 (C₄₂H₃₀ClNSSi = 644.30) Sub1-41 m/z = 823.16 (C₅₄H₃₄ClNS₂Si = 824.53) Sub 1-42 m/z = 629.19(C₄₂H₃₂ClNOSi = 630.26) Sub 1-43 m/z = 511.15 (C₃₄H₂₆ClNSi = 512.12) Sub1-44 m/z = 461.14 (C₃₀H₂₄ClNSi = 462.06) Sub 1-45 m/z = 585.17(C₄₀H₂₈ClNSi = 586.21) Sub 1-46 m/z = 511.15 (C₃₄H₂₆ClNSi = 512.12) Sub1-47 m/z = 511.15 (C₃₄H₂₆ClNSi = 512.12) Sub 1-48 m/z = 649.20(C₄₂H₃₆ClNSSi = 650.35) Sub 1-49 m/z = 661.20 (C₄₆H₃₂ClNSi = 662.30) Sub1-50 m/z = 551.15 (C₃₆H₂₆ClNOSi = 552.15) Sub 1-51 m/z = 611.18(C₄₂H₃₀ClNSi = 612.24) Sub 1-52 m/z = 611.18 (C₄₂H₃₀ClNSi = 612.24) Sub1-53 m/z = 537.17 (C₃₆H₂₈ClNSi = 538.16) Sub 1-54 m/z = 687.21(C₄₈H₃₄ClNSi = 688.34 Sub 1-55 m/z = 717.17 (C₄₈H₃₂ClNSSi = 718.39) Sub1-56 m/z = 661.20 (C₄₆H₃₂ClNSi = 662.30) Sub 1-57 m/z = 611.18(C₄₂H₃₀ClNSi = 612.24) Sub 1-58 m/z = 763.25 (C₅₄H₃₈ClNSi = 764.44) Sub1-59 m/z = 611.18 (C₄₂H₃₀ClNSi = 612.24) Sub 1-60 m/z = 767.19(C₅₂H₃₄ClNSSi = 768.45) Sub 1-61 m/z = 611.18 (C₄₂H₃₀ClNSi = 612.24) Sub1-62 m/z = 815.28 (C₅₈H₄₂ClNSi = 816.52)

Sub 2 of Scheme 1 may be synthesized as follows, but is not limitedthereto.

1. Synthesis Example of Sub 2-1

After dissolving bromobenzene (40.68 g, 259.09 mmol) in toluene (1360ml) in a round bottom flask, aniline (26.54 g, 285.00 mmol), Pd₂(dba)₃(7.12 g, 7.77 mmol), 50% P(t-Bu)₃ (10.1 ml, 20.73 mmol) and NaOt-Bu(74.70 g, 777.28 mmol) were added the solution, and the mixture wasstirred at 80° C. When the reaction was completed, the reaction productwas extracted with CH₂Cl₂ and water, the organic layer was dried withMgSO₄ and concentrated. Thereafter, the concentrate was separated by asilica gel column and recrystallized to obtain 32.88 g (yield: 75%) ofproduct Sub 2-1.

2. Synthesis Example of Sub 2-2

The reaction was carried out in the same manner as in the synthesismethod of Sub 2-1 using 4-bromo-1,1′-biphenyl (23.65 g, 101.46 mmol),aniline (10.39 g, 111.60 mmol), Pd₂(dba)₃ (2.79 g, 3.04 mmol), 50%P(t-Bu)₃ (4.0 ml, 8.12 mmol), NaOt-Bu (29.25 g, 304.38 mmol) and toluene(710 ml) to obtain 20.66 g (yield: 83%) of product Sub 2-2.

3. Synthesis Example of Sub 2-3

The reaction was carried out in the same manner as in the synthesismethod of Sub 2-1 using 2-bromodibenzo[b,d]thiophene (38.11 g, 144.82mmol), aniline (14.84 g, 159.30 mmol), Pd₂(dba)₃ (3.98 g, 4.34 mmol),50% P(t-Bu)₃ (5.6 ml, 11.59 mmol), NaOt-Bu (41.76 g, 434.47 mmol) andtoluene (760 ml) to obtain 30.7 g (yield: 77%) of product Sub 2-3.

4. Synthesis Example of Sub 2-26

The reaction was carried out in the same manner as in the synthesismethod of Sub 2-1 using 3-chloro-6-phenyldibenzo[b,d]thiophene (30 g,0.1 mol), benzen-d5-amine (10 g, 0.1 mol), Pd₂(dba)₃ (2.8 g, 0.03 mol),50% P(t-Bu)₃ (2.4 ml, 006 mol), NaOt-Bu (29.3 g, 0.3 mol) and toluene(200 ml) to obtain 32 g (yield: 88%) of product Sub 2-26.

Compounds belonging to Sub 2 prepared by the above synthesis example maybe the following compounds, but is not limited thereto, and Table 2shows the FD-MS value of the following compounds.

TABLE 2 Compound FD-MS Compound FD-MS Sub 2-1 m/z = 169.09 (C₁₂H₁₁N =169.23) Sub 2-2 m/z = 245.12 (C₁₈H₁₅N = 245.33) Sub 2-3 m/z = 275.08(C₁₈H₁₃NS = 275.37) Sub 2-4 m/z = 275.08 (C₁₈H₁₃NS = 275.37) Sub 2-5 m/z= 259.10 (C₁₈H13NO = 259.31) Sub 2-6 m/z = 259.10 (C₁₈H₁₃NO = 259.31)Sub 2-7 m/z = 275.08 (C₁₈H₁₃NS = 275.37) Sub 2-8 m/z = 334.15 (C₂₄H₁₈N₂=334.42) Sub 2-9 m/z = 352.10 (C₂₃H₁₆N₂S = 352.46) Sub 2-10 m/z = 351.11(C₂₄H₁₇NS = 351.47) Sub 2-11 m/z = 351.11 (C₂₄H₁₇NS = 351.47) Sub 2-12m/z = 359.13 (C₂₆H₁₇NO = 359.43) Sub 2-13 m/z = 309.12 (C₂₂H₁₅NO =309.37) Sub 2-14 m/z = 381.06 (C₂₄H₁₅NS₂= 381.51) Sub 2-15 m/z = 335.13(C₂₄H₁₇NO = 335.41) Sub 2-16 m/z = 325.09 (C₂₂H₁₅NS = 325.43) Sub 2-17m/z = 309.12 (C₂₂H₁₅NO = 309.37) Sub 2-18 m/z = 289.09 (C₁₉H₁₅NS =289.40) Sub 2-19 m/z = 309.12 (C₂₂H₁₅NO = 309.37) Sub 2-20 m/z = 325.09(C₂₂H₁₅NS = 325.43) Sub 2-21 m/z = 409.15 (C₃₀H₁₉NO = 409.49) Sub 2-22m/z = 349.11 (C₂₄H₁₅NO₂= 349.39) Sub 2-23 m/z = 440.13 (C₃₀H₂₀N₂S =440.56) Sub 2-24 m/z = 435.16 (C₃₂H₂₁NO = 435.53) Sub 2-25 m/z = 351.11(C₂₄H₁₇NS = 351.47) Sub 2-26 m/z = 356.14 (C₂₄H₁₂D₅NS = 356.50) Sub 2-27m/z = 375.16 (C₂₇H₂₁NO = 375.47) Sub 2-28 m/z = 385.15 (C₂₈H₁₉NO =385.47) Sub 2-29 m/z = 293.07 (C₁₈H₁₂FNS = 293.36) Sub 2-30 m/z = 413.15(C₂₈H₁₉N₃O = 413.48) Sub 2-31 m/z = 411.16 (C₃₀H₂₁NO = 411.50) Sub 2-32m/z = 409.15 (C₃₀H₁₉NO = 409.49) Sub 2-33 m/z = 285.15 (C₂₁H₁₉N =285.39) Sub 2-34 m/z = 411.16 (C₃₀H₂₁NO = 411.50)

Synthesis Example of Final Compound 1. Synthesis Example of P-1

After dissolving Sub 1-1 (10 g, 0.016 mol) in toluene (31 ml), Sub 2-1(2.6 g, 0.016 mol), Pd₂(dba)₃ (0.4 g, 0.0005 mmol), 50% P(t-Bu)₃ (0.4ml, 0.001 mmol) and NaOt-Bu (4.5 g, 0.05 mol) were added the solutionand the mixture was stirred at 130° C. When the reaction was completed,the reaction product was extracted with CH₂Cl₂ and water, the organiclayer was dried with MgSO₄ and concentrated. Thereafter, the concentratewas separated by a silica gel column and recrystallized to obtain 10 g(yield: 83%) of product P-1.

2. Synthesis Example of P-13

The reaction was carried out in the same manner as in the synthesismethod of P-1 using Sub 1-5 (13 g, 0.024 mol), Sub 2-10 (8.5 g, 0.024mol), Pd₂(dba)₃ (0.7 g, 0.0007 mol), P(t-Bu)₃ (0.6 mL, 0.0007 mmol),NaOt-Bu (7 g, 0.07 mol) and toluene (31 ml) to obtain 17 g (yield: 82%)of product P-13.

3. Synthesis Example of P-22

The reaction was carried out in the same manner as in the synthesismethod of P-1 using Sub 1-17 (12 g, 0.02 mol), Sub 2-23 (9.8 g, 0.02mol), Pd₂(dba)₃ (0.61 g, 0.0007 mol), P(t-Bu)₃ (0.5 mL, 0.001 mmol),NaOt-Bu (6.4 g, 0.06 mol) and toluene (33 ml) to obtain 17 g (yield:80%) of product P-22.

4. Synthesis Example of P-59

The reaction was carried out in the same manner as in the synthesismethod of P-1 using Sub 1-42 (15 g, 0.023 mol), Sub 2-5 (6.2 g, 0.023mmol), Pd₂(dba)₃ (0.65 g, 0.0007 mol), P(t-Bu)₃ (0.6 mL, 0.001 mol),NaOt-Bu (6.9 g, 0.07 mol) and toluene (35 ml) to obtain 18 g (yield:83.6%) of product P-59.

5. Synthesis Example of P-73

The reaction was carried out in the same manner as in the synthesismethod of P-1 using Sub 1-51 (12 g, 0.016 mol), Sub 2-1 (2.8 g, 0.016mmol), Pd₂(dba)₃ (0.46 g, 0.0005 mol), P(t-Bu)₃ (0.4 mL, 0.001 mmol) andNaOt-Bu (4.8 g, 0.05 mol) to obtain 11 g (yield: 77%) of product P-72.

The FD-MS values of compounds P-1 to P-80 of the present inventionprepared according to the above synthesis examples are shown in Table 3below.

TABLE 3 Compound FD-MS Compound FD-MS P-1 m/z = 774.25(C₅₄H₃₈N₂SSi =775.06) P-2 m/z = 774.25 (C₅₄H₃₈N₂SSi = 775.06) P-3 m/z =758.28(C₅₄H₃₈N₂OSi = 759.0) P-4 m/z = 758.28(C₅₄H₃₈N₂OSi = 759.0) P-5m/z = 774.25(C₅₄H₃₈N₂SSi = 775.06) P-6 m/z = 774.25 (C₅₄H₃₈N₂SSi =775.06) P-7 m/z = 758.28(C₅₄H₃₈N₂OSi = 759.0) P-8 m/z =758.28(C₅₄H₃₈N₂OSi = 759.0) P-9 m/z = 878.32(C₆₂H₄₆N₂SSi = 879.2) P-10m/z = 726.25(C₅₀H₃₈N₂SSi = 727.0) P-11 m/z = 986.37(C₇₂H₅₀N₂OSi = 987.3)P-12 m/z = 808.29(C₅₈H₄₀N₂OSi = 809.1) P-13 m/z = 85O.28(C₆₀H₄₂N₂SSi =851.2) P-14 m/z = 878.32(C₆₂H₄₆N₂SSi = 879.21) P-15 m/z =886.34(C₆₄H₄₆N₂OSi = 887.2) P-16 m/z = 808.29(C₅₈H₄₀N₂OSi = 809.1) P-17m/z = 764.27(C₅₃H₄₀N₂SSi = 765.1) P-18 m/z = 664.24(C₄₅H₃₆N₂SSi =664.94) P-19 m/z = 754.25(C₅₁H₃₈N₂OSSi = 755.0) P-20 m/z =648.26(C₄₅H₃₆N₂OSi = 648.9) P-21 m/z = 756.21(C₅₀H₃₆N₂S₂Si = 757.1) P-22m/z = 939.31(C₆₆H₄₅N₃SSi = 940.25) P-23 m/z = 812.32(C₅₈H₄₄N₂OSi =813.1) P-24 m/z = 974.37(C₇₁H₅₀N₂OSi = 975.3) P-25 m/z =88O.24(C₆₀H₄₀N₂S₂Si = 881.2) P-26 m/z = 818.22(C₅₅H₃₈N₂S₂Si = 819.1)P-27 m/z = 862.30(C₆₁H₄₂N₂O₂Si = 863.10) P-28 m/z = 740.23(C₅₀H₃₆N₂OSSi= 741.00) P-29 m/z = 851.28(C₅₉H₄₁N₃SSi = 852.1) P-30 m/z =939.31(C₆₆H₄₅N₃SSi = 940.25) P-31 m/z = 910.34(C₆₆H₄₆N₂OSi = 911.2) P-32m/z = 987.36(C₇₁H₄₉N₃OSi = 988.3) P-33 m/z = 910.3(C₆₂H₄₆N₂O₂SSi =911.2) P-34 m/z = 865.29(C₆₀H₄₃N₃SSi = 866.17) P-35 m/z =710.28(C₅₀H₃₈N₂OSi = 711.0) P-36 m/z = 1008.4(C₇₄H₄₈N₂OSi = 1009.3) P-37m/z = 880.24(C₆₀H₄₀N₂S₂Si = 881.2) P-38 m/z = 874.28(C₆₂H₄₂N₂SSi =875.18) P-39 m/z = 858.31(C₆₂H₄₂N₂OSi = 859.1) P-40 m/z =786.31(C₅₆H₄₂N₂OSi = 787.1) P-41 m/z = 986.23(C₆₆H₄₂N₂S₃Si = 987.3) P-42m/z = 88O.24(C₆₀H₄₀N₂S₂Si = 881.2) P-43 m/z = 848.29(C₆₀H₄₀N₂)₂Si =849.08) P-44 m/z = 834.31(C₆₀H₄₂N₂OSi = 835.1) P-45 m/z =815.28(C₅₆H₄₁N₃SSi = 816.1) P-46 m/z = 951.31(C₆₇H₄₅N₃SSi = 952.26) P-47m/z = 724.29(C₅₁H₄₀N₂OSi = 725.0) P-48 m/z = 849.32(C₆₀H₄₃N₃OSi = 850.1)P-49 m/z = 951.33(C₆₇H₄₅N₃O₂Si = 952.20) P-50 m/z = 837.3(C₅₆H₃₅D₅N₂S₂Si= 838.2) P-51 m/z = 774.27(C₅₄H₃₈N₂O₂Si = 775.00) P-52 m/z =1075.4(C₇₈H₅₃N₃OSi = 1076.4) P-53 m/z = 824.27(C₅₈H₄₀N₂SSi = 825.12)P-54 m/z = 824.27(C₅₈H₄₀N₂SSi = 825.12) P-55 m/z = 808.29(C₅₈H₄₀N₂OSi =809.1) P-56 m/z = 808.29(C₅₈H₄₀N₂OSi = 809.1) P-57 m/z =866.28(C₆₀H₄₂N₂OSSi = 867.2) P-58 m/z = 1076.3(C₇₃H₄₈N₂S₃Si = 1077.5)P-59 m/z = 852.32(C₆₀H₄₄N₂O₂Si = 853.11) P-60 m/z = 886.34(C₆₄H₄₆N₂OSi =887.17) P-61 m/z = 700.24(C₄₈H₃₆N2SSi = 701.0) P-62 m/z =842.26(C₅₈H₃₉FN₂SSi = 843.1) P-63 m/z = 734.3(C₅₂H₃₈N₂OSi = 734.97) P-64m/z = 888.33(C₆₂H₄₄N₄OSi = 889.15) P-65 m/z = 888.30(C₆₀H₄₈N₂S₂Si =889.3) P-66 m/z = 950.32(C₆₈H₄₆N₂SSi = 951.28) P-67 m/z =684.26(C₄₈H₃₆N₂OSi = 684.9) P-68 m/z = 900.32 (C₆₄H₄₄N₂O₂Si = 901.2)P-69 m/z = 850.28(C₆₀H₄₂N₂SSi = 851.16) P-70 m/z = 850.28(C₆₀H₄₂N₂SSi =851.16) P-71 m/z = 810.31 (C₅₈H₄₂N₂OSi = 811.1) P-72 m/z =910.34(C₆₆H₄₆N₂OSi = 911.2) P-73 m/z = 85O.28(C₆₀H₄₂N₂SSi = 851.2) P-74m/z = 900.30(C₆₄H₄₄N₂SSi = 901.22) P-75 m/z = 834.31(C₆₀H₄₂N₂OSi =835.1) P-76 m/z = 1062.4(C₇₈H₅₄N₂OSi = 1063.4) P-77 m/z =850.28(C₆₀H₄₂N₂SSi = 851.1) P-78 m/z = 900.3(C₆₄H₄₄N₂SSi = 901.22) P-79m/z = 834.3(C₆₀H₄₂N₂OSi = 835.09) P-80 m/z = 1064.45(C₇₉H₆₀N₂Si =1065.5)

Manufacturing and Evaluation of Organic Electric Element

[Example 1] Red Organic Electroluminescent Element (AnEmission-Auxiliary Layer)

N¹-(naphthalen-2-yl)-N⁴,N⁴-bis(4-(naphthalen-2-yl(phenyl)amino)phenyl)-N¹-phenylbenzene-1,4-diamine (hereinafter, “2-TNATA”) on an ITO layer (anode)formed on a glass substrate was vacuum-deposited to a thickness of 60 nmto form a hole injection layer. Thereafter, N,N′-bis(1-naphthalenyl)-N,N′-bis-phenyl-(1,1′-biphenyl)-4,4′-diamine (hereinafter, “NPB”) on thehole injection layer was vacuum-deposited to a thickness of 60 nm toform a hole transport layer.

Subsequently, after an emission-auxiliary layer with a thickness of 20nm was formed by vacuum-depositing the compound P-1 of the presentinvention on the hole transport layer,4,4′-N,N′-dicarbazole-biphenyl(hereinafter, “CBP”) as a host materialand bis-(1-phenylisoquinoly)iridium(III)acetylacetonate (hereinafter,“(piq)₂Ir(acac)”) as a dopant material in a weight ratio of 95:5 weredeposited on the emission-auxiliary layer to form a light emitting layerwith a thickness of 30 nm.

Subsequently,(1,1′-bisphenyl-4-olato)bis(2-methyl-8-quinolinolato)aluminum(hereinafter, “BAIq”) was vacuum-deposited to a thickness of 5 nm on thelight emitting layer to form a hole blocking layer, andtris-(8-hydroxyquinoline)aluminum (hereinafter, “Alq₃”) wasvacuum-deposited to a thickness of 40 nm on the hole blocking layer toform a an electron transport layer. Thereafter, LiF was deposited to athickness of 0.2 nm to form an electron injection layer, and then Al wasdeposited to a thickness of 150 nm to form a cathode.

[Example 2 to Example 13] Red Organic Electroluminescent Element (AnEmission-Auxiliary Layer)

The organic electroluminescent elements were manufactured in the samemanner as described in Example 1 except that compounds of the presentinvention described in the following Table 4 instead of compound P-1 ofthe present invention, were used as material of an emission-auxiliarylayer.

[Comparative Example 1] to [Comparative Example 3]

The organic electroluminescent elements were manufactured in the samemanner as described in Example 1 except that Comparative Compound A to Cwere used as material of an emission-auxiliary layer, respectively.

Electroluminescence (EL) characteristics were measured with PR-650(Photo esearch) by applying a forward bias DC voltage to the organicelectroluminescent elements prepared in Examples 1 to 13 of the presentinvention and Comparative Examples 1 to 3. And, the T95 life time wasmeasured using a life time measuring apparatus manufactured by msscience Inc. at reference brightness of 2500 cd/m². The measurementresults are shown in Tables 4 below.

TABLE 4 Current Voltage Density Brightness Efficiency Lifetime CIECompound (V) (mA/cm²) (cd/m²) (cd/A) T(95) x y comp. Ex(1) comp. Com A6.5 32.1 2500.0 7.8 30.1 0.62 0.33 comp. Ex(2) comp. Com B 6.6 30.12500.0 8.3 50.8 0.63 0.30 comp. Ex(3) comp. Com C 6.3 27.5 2500.0 9.145.2 0.60 0.33 Ex.(1) P-1 5.5 16.1 2500.0 15.5 73.2 0.63 0.34 Ex.(2) P-45.5 16.5 2500.0 15.1 70.3 0.64 0.33 Ex.(3) P-6 5.5 16.4 2500.0 15.3 72.40.64 0.35 Ex.(4) P-12 5.5 16.6 2500.0 15.1 79.9 0.62 0.32 Ex.(5) P-145.6 16.9 2500.0 14.8 71.0 0.63 0.30 Ex.(6) P-21 5.8 18.7 2500.0 13.464.5 0.64 0.31 Ex.(7) P-38 5.7 17.5 2500.0 14.3 76.6 0.61 0.35 Ex.(8)P-44 5.7 17.2 2500.0 14.5 77.5 0.62 0.34 Ex.(9) P-55 6.0 19.5 2500.012.8 80.2 0.62 0.32 Ex.(10) P-62 5.6 16.7 2500.0 14.9 76.9 0.65 0.33Ex.(11) P-67 5.9 18.0 2500.0 13.9 68.1 0.62 0.34 Ex.(12) P-73 5.6 17.02500.0 14.7 74.0 0.62 0.35 Ex.(13) P-75 5.6 16.9 2500.0 14.8 73.2 0.650.33

From the results of Table 4, it is can be seen that not only can thedriving voltage be lowered, but efficiency and lifespan aresignificantly improved where a red organic electric element aremanufactured using the compound of the present invention as material foran emission-auxiliary layer, compared to the cases of using ComparativeCompounds A to C.

The present invention is the same as the comparative compound in thatthe amine groups are bonded to both benzene ring of the dibenzosilolecore, respectively, but the present invention is different in that aminegroup is substituted with the specific substituents such asdibenzothiophen or dibenzofuran.

Where dibenzothiophen or dibenzofuran is introduced as substituent ofamine group, the refractive index is significantly increased and the Tgvalue is also increased, compare to the case where the substituent suchas a general aryl group or the substituents in Comparative Compound B orComparative Compound C is introduced. Therefore, in accordance with theembodiment of the present invention, it seems that luminous efficiencyand thermal stability are improved, and thus, the lifespan and the likeis increased.

This is because even though core of compound is the same, the physicalproperties of the compound are different depending on the type of thesubstituent substituted on the amino group. This suggests that thedifference of properties may act as a major factor in improving theperformance of the device when depositing the compound.

Although the exemplary embodiments of the present invention have beendescribed for illustrative purposes, those skilled in the art to whichthe present invention pertains will be capable of various modificationswithout departing from the essential characteristics of the presentinvention. Therefore, the embodiment disclosed herein is intended toillustrate the scope of the technical idea of the present invention, andthe spirit and scope of the present invention are not limited by theembodiments. The scope of the present invention shall be construed onthe basis of the accompanying claims, and it shall be construed that allof the technical ideas included within the scope equivalent to theclaims belong to the present invention.

The invention claimed is:
 1. A compound represented by one of Formula 8to 10:

wherein: Ar₁ and Ar₂ are each independently selected from the groupconsisting of a C₆-C₆₀ aryl group, a C₂-C₆₀ heterocyclic groupcontaining at least one heteroatom of O, N, S, Si, and P, a C₃-C₆₀aliphatic ring group, a C₁-C₅₀ alkyl group, a C₂-C₂₀ alkenyl group, aC₂-C₂₀ alkynyl group, a C₁-C₃₀ alkoxyl group, a C₆-C₃₀ aryloxy group,and -L′-N(R_(a))(R_(b)), and adjacent groups together may be bonded toeach other to form a heterocyclic group containing Si, Ar₃ to Ar₆ areeach independently selected from the group consisting of a C₆-C₆₀ arylgroup, a C₂-C₆₀ heterocyclic group containing at least one heteroatom ofO, N, S, Si, and P, a C₃-C₆₀ aliphatic ring group, -L′-N(R_(a))(R_(b))and Formula 1-1, and adjacent groups together may be bonded to eachother to form a heterocyclic group containing N, with the proviso thatat least one of Ar₃ to Ar₆ is Formula 1-1,

X is O or S, R₁ and R₂ are each independently selected from the groupconsisting of hydrogen, deuterium, halogen, a C₆-C₆₀ aryl group, afluorenyl group, a C₂-C₆₀ heterocyclic group containing at least oneheteroatom of O, N, S, Si, and P, a C₃-C₆₀ aliphatic ring group, aC₁-C₅₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₁-C₃₀ alkoxyl group, aC₆-C₃₀ aryloxy group and -L′-N(R_(a))(R_(b)), R₃ and R₄ are eachindependently selected from the group consisting of hydrogen, deuterium,halogen, a C₆-C₆₀ aryl group, a fluorenyl group, a C₂-C₆₀ heterocyclicgroup containing at least one heteroatom of O, N, S, Si, and P, a C₃-C₆₀aliphatic ring group, a C₁-C₅₀ alkyl group, a C₂-C₂₀ alkenyl group, aC₁-C₃₀ alkoxyl group, a C₆-C₃₀ aryloxy group and -L′-N(R_(a))(R_(b)),and adjacent groups together may be bonded to each other to form a ring,n, m and o are each an integer of 0 to 3, l is an integer of 0 to 4,where they are each an integer of 2 or more, each of a plurality of R₁s,each of a plurality of R₂s, each of a plurality of R₃s, each of aplurality of R₄s are the same or different from each other, L₁, L₂ and Lare each independently selected from the group consisting of a singlebond, a C₆-C₆₀ arylene group, a fluorenylene group, a C₂-C₆₀heterocyclic group containing at least one heteroatom of O, N, S, Si,and P, and a C₃-C₆₀ aliphatic ring group, L′ is selected from the groupconsisting of a single bond, a C₆-C₆₀ arylene group, a fluorenylenegroup, a C₃-C₆₀ aliphatic ring and a C₂-C₆₀ heterocyclic group, R_(a)and R_(b) are each independently selected from the group consisting of aC₆-C₆₀ aryl group, a fluorenyl group, a C₃-C₆₀ aliphatic ring group, anda C₂-C₆₀ heterocyclic group containing at least one heteroatom of O, N,S, Si, and P, and Ar₁ to Ar₆, R₁ to R₄, the ring formed by adjacentgroups, L₁, L₂, L, L′, R_(a) and R_(b) may be each optionallysubstituted with one or more substituents selected from the groupconsisting of deuterium, halogen, a silane group unsubstituted orsubstituted with a C₁-C₂₀ alkyl group or a C₆-C₂₀ aryl group, a siloxanegroup, a boron group, a germanium group, a cyano group, a nitro group, aphosphine oxide group unsubstituted or substituted with a C₁-C₂₀ alkylgroup or a C₆-C₂₀ aryl group, a C₁-C₂₀ alkylthio group, a C₁-C₂₀ alkoxylgroup, a C₁-C₂₀ alkyl group, a C₂-C₂₀ alkenyl group, a C₂-C₂₀ alkynylgroup, a C₆-C₂₀ aryl group, a C₆-C₂₀ aryl group substituted withdeuterium, a fluorenyl group, a C₂-C₂₀ heterocyclic group containing atleast one heteroatom of O, N, S, Si, and P, a C₃-C₂₀ cycloalkyl group, aC₇-C₂₀ arylalkyl group, and C₈-C₂₀ arylalkenyl group.
 2. An organicelectric element comprising a first electrode, a second electrode, andan organic material layer formed between the first electrode and thesecond electrode, wherein the organic material layer comprises a singlecompound two or more compounds represented by Formula 1 of claim
 1. 3.The organic electric element of claim 2, wherein the organic materiallayer comprises at least one of a hole injection layer, a hole transportlayer, an emission-auxiliary layer, a light emitting layer, an electrontransport-auxiliary layer, an electron transport layer and an electroninjection layer.
 4. The organic electric element of claim 3, wherein thecompound is comprised in the hole transport layer or theemission-auxiliary layer.
 5. The organic electric element of claim 2,wherein the organic material layer is formed by spin coating, nozzleprinting, inkjet printing, slot coating, dip coating or roll-to-roll. 6.An electronic device comprising a display device and a control unit fordriving the display device, wherein the display device comprises theorganic electric element of claim
 2. 7. The electronic device of claim6, wherein the organic electric element is selected from the groupconsisting of an organic electroluminescent element, an organic solarcell, an organic photo conductor, an organic transistor, an element formonochromatic illumination and element for quantum dot display.
 8. Acomposition comprising one of the following compounds:


9. An organic electric element comprising a first electrode, a secondelectrode, and an organic material layer formed between the firstelectrode and the second electrode, wherein the organic material layercomprises the composition of claim
 8. 10. An electronic devicecomprising a display device and a control unit for driving the displaydevice, wherein the display device comprises the organic electricelement of claim 9.